Oprah, Ivanka, and More in City's Newly Released Cathie Black Emails

As we reported yesterday, the Bloomberg administration lost its lengthy and expensive legal battle against a Freedom of Information Law request by Sergio Hernandez, then a Village Voice intern, requesting the administration's emails concerning the ill-fated hiring of former Schools Chancelor Cathie Black in 2010.

Well, now the emails have been released. And while it's hard to see what was so damning in the emails that the City saw fit to spend tens of thousands of dollars fighting to keep them secret, there's still plenty of interesting material inside. The emails, between Black and various administration aids and officials, illuminate the public relations campaign City Hall orchestrated to help smooth the way for its unpopular and inexplicable nomination of Black, who had no previous educational experience.

The strategy is best summed up by an email from Micah Lasher, at the time the mayor's legislative director: "All our focus needs to be on getting allies to come out in support."

The list of allies approached and considered is somewhat amusing. Among those solicited for support: Gloria Steinem, Geraldine Ferraro, Nora Ephron, Suze Orman, Deborah Norville, and, most notably, Oprah Winfrey. Lobbied hard and supplied with flattering talking points by the administration, Winfrey did end up endorsing Black as Schools Chancelor, leading to a Daily News cover headline that read: "O Backs Cathie: Talk-show queen gushes over Bloomie's controversial pick" Stu Loeser, the mayor's press secretary at the time, was pleased, emailing, "I was surprised to learn we succeded in have Oprah knock a crime story off the cover of the news today."

Other targeted endorsements didn't go so well. Black, who had met Caroline Kennedy once, emailed her shortly before 6 a.m. November 18, asking for her to sign a letter of support. By that afternoon, she sent an anxious email noting she still hadn't heard back. The same day, Black also volunteered a testimonial from the Donald-Spawn: "Would we want Ivanka Trump? Think she would do," she wrote Lasher. "I would skip," he responded curtly. Burrrrrn, Ivanka.